Regan grew up in Portland, Maine and attended Deering High School where he played on the varsity baseball, basketball, football and golf teams. He was drafted out of high school by the Seattle Mariners but opted to attend Vanderbilt University where he played baseball for two years. He continued his education at Western Kentucky University where he held a 3.8 GPA and was captain of the baseball team. He graduated in 2014 with a degree in Financial Management. Regan has been working in the financial services industry since graduation and is licensed with his Series 7.
Regan enjoys spending time with his father, Ed, who is the baseball coach at the University of Southern Maine and watching his brother, Ryan, play infield for the Baltimore Orioles. When he is not spending time with his family, he is playing golf or enjoying time with his friends.